CA3016830C - Crystalline forms of mesylate salt of pyridinyl amino pyrimidine derivative, preparation methods therefor, and applications thereof - Google Patents
Crystalline forms of mesylate salt of pyridinyl amino pyrimidine derivative, preparation methods therefor, and applications thereof Download PDFInfo
- Publication number
- CA3016830C CA3016830C CA3016830A CA3016830A CA3016830C CA 3016830 C CA3016830 C CA 3016830C CA 3016830 A CA3016830 A CA 3016830A CA 3016830 A CA3016830 A CA 3016830A CA 3016830 C CA3016830 C CA 3016830C
- Authority
- CA
- Canada
- Prior art keywords
- crystalline forms
- mesylate salt
- applications
- preparation methods
- pyrimidine derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title abstract 3
- RHXVSZXHWDQESH-UHFFFAOYSA-N 4-pyridin-2-ylpyrimidin-2-amine Chemical class NC1=NC=CC(C=2N=CC=CC=2)=N1 RHXVSZXHWDQESH-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 241000124008 Mammalia Species 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical class FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention provides crystalline form I and crystalline form II of a mesylate salt of a pyridinyl amino pyrimidine derivative and preparation methods therefor, a pharmaceutical composition containing the crystalline forms, and applications of the crystalline forms in the treatment of activated EGFR mutant- or drug-resistant mutant-mediated diseases, especially cancer, in mammals, particularly humans. The crystalline forms of the mesylate salt of the compound represented by formula (I) have good solubility and high bioavailability in animals.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610127022.3 | 2016-03-07 | ||
| CN201610127022.3A CN107163027B (en) | 2016-03-07 | 2016-03-07 | The crystal form of pyridine amine pyrimidine derivates mesylate and its preparation and application |
| PCT/CN2017/000203 WO2017152707A1 (en) | 2016-03-07 | 2017-03-01 | Crystalline forms of mesylate salt of pyridinyl amino pyrimidine derivative, preparation methods therefor, and applications thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA3016830A1 CA3016830A1 (en) | 2017-09-14 |
| CA3016830C true CA3016830C (en) | 2021-05-18 |
Family
ID=59788981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3016830A Active CA3016830C (en) | 2016-03-07 | 2017-03-01 | Crystalline forms of mesylate salt of pyridinyl amino pyrimidine derivative, preparation methods therefor, and applications thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10550101B2 (en) |
| EP (1) | EP3428159B1 (en) |
| JP (1) | JP6894917B2 (en) |
| KR (1) | KR102142797B1 (en) |
| CN (2) | CN107163027B (en) |
| CA (1) | CA3016830C (en) |
| ES (1) | ES2863923T3 (en) |
| PL (1) | PL3428159T3 (en) |
| WO (1) | WO2017152707A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105315259B (en) * | 2014-07-29 | 2018-03-09 | 上海艾力斯医药科技有限公司 | Pyridine amine pyrimidine derivates, its preparation method and application |
| CN107163026B (en) | 2016-03-07 | 2019-07-02 | 上海艾力斯医药科技有限公司 | The salt and its preparation method and application of pyridine amine pyrimidine derivates |
| CN110606841A (en) * | 2018-06-15 | 2019-12-24 | 上海艾力斯医药科技有限公司 | Crystal form of pyridylamino pyrimidine derivative and preparation method thereof |
| CN112292378B (en) * | 2019-05-22 | 2024-02-06 | 上海翰森生物医药科技有限公司 | Indole derivative-containing inhibitor, preparation method and application thereof |
| WO2023035223A1 (en) * | 2021-09-10 | 2023-03-16 | 上海艾力斯医药科技股份有限公司 | Pharmaceutical composition and use thereof |
| US20230416255A1 (en) * | 2022-06-27 | 2023-12-28 | Abion Inc. | Mesylate salts of triazolopyrazine derivatives |
| CN116478138A (en) * | 2023-04-21 | 2023-07-25 | 江苏艾力斯生物医药有限公司 | Crystallization method of vomertinib mesylate bulk drug |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2900230T3 (en) * | 2011-07-27 | 2022-03-16 | Astrazeneca Ab | 2-(2,4,5-anilino substituted)pyrimidine compounds |
| CN104761544B (en) * | 2014-01-03 | 2019-03-15 | 北京轩义医药科技有限公司 | The selective depressant of the important mutant of clinic of EGFR tyrosine kinase |
| CN105315259B (en) * | 2014-07-29 | 2018-03-09 | 上海艾力斯医药科技有限公司 | Pyridine amine pyrimidine derivates, its preparation method and application |
| CN107163026B (en) * | 2016-03-07 | 2019-07-02 | 上海艾力斯医药科技有限公司 | The salt and its preparation method and application of pyridine amine pyrimidine derivates |
-
2016
- 2016-03-07 CN CN201610127022.3A patent/CN107163027B/en active Active
- 2016-03-07 CN CN201911024029.2A patent/CN110590749B/en active Active
-
2017
- 2017-03-01 ES ES17762393T patent/ES2863923T3/en active Active
- 2017-03-01 KR KR1020187028799A patent/KR102142797B1/en active IP Right Grant
- 2017-03-01 EP EP17762393.1A patent/EP3428159B1/en active Active
- 2017-03-01 US US16/083,210 patent/US10550101B2/en active Active
- 2017-03-01 WO PCT/CN2017/000203 patent/WO2017152707A1/en active Application Filing
- 2017-03-01 CA CA3016830A patent/CA3016830C/en active Active
- 2017-03-01 JP JP2018547272A patent/JP6894917B2/en active Active
- 2017-03-01 PL PL17762393T patent/PL3428159T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN107163027B (en) | 2019-11-05 |
| EP3428159A1 (en) | 2019-01-16 |
| ES2863923T3 (en) | 2021-10-13 |
| JP6894917B2 (en) | 2021-06-30 |
| US20190092753A1 (en) | 2019-03-28 |
| CA3016830A1 (en) | 2017-09-14 |
| JP2019507776A (en) | 2019-03-22 |
| US10550101B2 (en) | 2020-02-04 |
| CN110590749A (en) | 2019-12-20 |
| EP3428159A4 (en) | 2019-08-07 |
| WO2017152707A1 (en) | 2017-09-14 |
| KR20180114227A (en) | 2018-10-17 |
| PL3428159T3 (en) | 2021-08-02 |
| EP3428159B1 (en) | 2021-01-27 |
| KR102142797B1 (en) | 2020-08-10 |
| CN110590749B (en) | 2020-11-06 |
| CN107163027A (en) | 2017-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190704 |